8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor
There have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopt...
| Main Authors: | , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2007-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Online Access: | https://doi.org/10.1186/1860-5397-3-1 |
| _version_ | 1818616006206029824 |
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| author | Thomas A. Munro Katharine K. Duncan Richard J. Staples Wei Xu Lee-Yuan Liu-Chen Cécile Béguin William A. Carlezon Jr. Bruce M. Cohen |
| author_facet | Thomas A. Munro Katharine K. Duncan Richard J. Staples Wei Xu Lee-Yuan Liu-Chen Cécile Béguin William A. Carlezon Jr. Bruce M. Cohen |
| author_sort | Thomas A. Munro |
| collection | DOAJ |
| description | There have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopts a boat conformation with the furan equatorial. Several lines of evidence suggest that epimerization proceeds via enolization of the lactone rather than a previously proposed indirect mechanism. Consistent with the general trend in related compounds, the title compound showed lower affinity at the kappa opioid receptor than the natural epimer salvinorin B (2a). The related 8-epi-acid 4b showed no affinity. |
| first_indexed | 2024-12-16T16:42:56Z |
| format | Article |
| id | doaj.art-9f810eb341a9481ab86113fa8452e2f7 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T16:42:56Z |
| publishDate | 2007-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-9f810eb341a9481ab86113fa8452e2f72022-12-21T22:24:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972007-01-0131110.1186/1860-5397-3-11860-5397-3-18-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptorThomas A. Munro0Katharine K. Duncan1Richard J. Staples2Wei Xu3Lee-Yuan Liu-Chen4Cécile Béguin5William A. Carlezon Jr.6Bruce M. Cohen7Mailman Research Center, McLean Hospital, 115 Mill St, Belmont MA 02478-9106, USAMailman Research Center, McLean Hospital, 115 Mill St, Belmont MA 02478-9106, USADepartment of Chemistry and Chemical Biology, Harvard University, Cambridge MA 02138, USADepartment of Pharmacology, Temple University, 3420 N. Broad Street, Philadelphia, PA 19140, USADepartment of Pharmacology, Temple University, 3420 N. Broad Street, Philadelphia, PA 19140, USAMailman Research Center, McLean Hospital, 115 Mill St, Belmont MA 02478-9106, USAMailman Research Center, McLean Hospital, 115 Mill St, Belmont MA 02478-9106, USAMailman Research Center, McLean Hospital, 115 Mill St, Belmont MA 02478-9106, USAThere have been many reports of epimerization of salvinorins at C-8 under basic conditions, but little evidence has been presented to establish the structure of these compounds. We report here the first crystal structure of an 8-epi-salvinorin or derivative: the title compound, 2b. The lactone adopts a boat conformation with the furan equatorial. Several lines of evidence suggest that epimerization proceeds via enolization of the lactone rather than a previously proposed indirect mechanism. Consistent with the general trend in related compounds, the title compound showed lower affinity at the kappa opioid receptor than the natural epimer salvinorin B (2a). The related 8-epi-acid 4b showed no affinity.https://doi.org/10.1186/1860-5397-3-1 |
| spellingShingle | Thomas A. Munro Katharine K. Duncan Richard J. Staples Wei Xu Lee-Yuan Liu-Chen Cécile Béguin William A. Carlezon Jr. Bruce M. Cohen 8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor Beilstein Journal of Organic Chemistry |
| title | 8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor |
| title_full | 8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor |
| title_fullStr | 8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor |
| title_full_unstemmed | 8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor |
| title_short | 8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor |
| title_sort | 8 epi salvinorin b crystal structure and affinity at the κ opioid receptor |
| url | https://doi.org/10.1186/1860-5397-3-1 |
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